In terms of maintenance, you should always have $2,000 in reserve. Tires will run $600-$1,000. Clutch will run $1,500 and will go out at the worst possible moment. Brakes $500. Engine CEL (MAF or O2 sensors) $300-$800.
And yes, you are likely to need to do about half of above list of items (or equiv) in the first 24 months of ownership of a 10-yr old car.
You'll have to make up your own mind on the IMS issue.
With all of that being said, if you decide to get a Boxster, you will be one of the happiest persons on earth.